Visible-Light Mediated Oxidative Fragmentation of Ethers and Acetals by Means of Fe(III) Catalysis

被引：16

作者：

Lindroth, Rickard ^{[1
]}

Ondrejkova, Alica ^{[1
]}

Wallentin, Carl-Johan ^{[1
]}

机构：

[1] Univ Gothenburg, Dept Chem & Mol Biol, SE-41296 Gothenburg, Sweden

来源：

ORGANIC LETTERS | 2022年 / 24卷 / 08期

基金：

瑞典研究理事会;

关键词：

REGIOSPECIFIC SYNTHESIS; BETA-CYCLODEXTRIN; COMPLEXES; CLEAVAGE; CYCLOALKANOLS; MECHANISM;

D O I：

10.1021/acs.orglett.2c00231

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new method employing iron(III) acetylacetonate along with visible light is described to effect oxidative ring opening of cyclic ethers and acetals with unparalleled efficiency. The method allows for a photocatalytic radical chemistry approach to functionalize relatively inert cyclic ethers into useful synthetic intermediates. The methodology sheds further light on the use of underexplored iron complexes in visible-light photochemical contexts and illustrates that simple Fe(III) complexes can initiate redox processes from (LMCT)-L-4 excited states.

引用

页码：1662 / 1667

页数：6

共 36 条

[1] MECHANISM AND SYNTHETIC UTILITY OF OXIDATIVE CLEAVAGE OF ETHERS BY AQUEOUS BROMINE [J].

DENO, NC ;

POTTER, NH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (14) :3550-&

[2]

ELAD D, 1963, TETRAHEDRON LETT, P2189

[3] Regiospecific synthesis of distally chlorinated ketones via C-C bond cleavage of cycloalkanols [J].

Fan, Xuefeng ;

Zhao, Huijun ;

Yu, Jiajia ;

Bao, Xiaoguang ;

Zhu, Chen .

ORGANIC CHEMISTRY FRONTIERS, 2016, 3 (02) :227-232

[4] No photocatalyst required - versatile, visible light mediated transformations with polyhalomethanes [J].

Franz, Johannes F. ;

Kraus, Wolfgang B. ;

Zeitler, Kirsten .

CHEMICAL COMMUNICATIONS, 2015, 51 (39) :8280-8283

[5] An Investigation into the One-Pot Heck Olefination-Hydrogenation Reaction [J].

Geoghegan, Kimberly ;

Kelleher, Susan ;

Evans, Paul .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (07) :2187-2194

[6] Organocatalytic Enantioselective Alkylation of Aldehydes with [Fe(bpy)3]Br2 Catalyst and Visible Light [J].

Gualandi, Andrea ;

Marchini, Marianna ;

Mengozzi, Luca ;

Natali, Mirco ;

Lucarini, Marco ;

Ceroni, Paola ;

Cozzi, Pier Giorgio .

ACS CATALYSIS, 2015, 5 (10) :5927-5931

[7] Investigation of Dopamine Analogues: Synthesis, Mechanistic Understanding, and Structure-Property Relationship [J].

Hu, Huamin ;

Dyke, Jason Christopher ;

Bowman, Brett Allen ;

Ko, Ching-Chang ;

You, Wei .

LANGMUIR, 2016, 32 (38) :9873-9882

[8] Manganese-catalyzed ring-opening chlorination of cyclobutanols: regiospecific synthesis of γ-chloroketones [J].

Huan, Leitao ;

Zhu, Chen .

ORGANIC CHEMISTRY FRONTIERS, 2016, 3 (11) :1467-1471

[9] Three-component aminoselenation of alkenes via visible-light enabled Fe-catalysis [J].

Huang, Binbin ;

Li, Yanan ;

Yang, Chao ;

Xia, Wujiong .

GREEN CHEMISTRY, 2020, 22 (09) :2804-2809

[10] Novel Preparation of H1 Receptor Antagonist Fexofenadine [J].

Huang, Jun ;

Wang, Wen ;

Wang, Li-Xin .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2010, 14 (06) :1472-1476

← 1 2 3 4 →